The food in the grocery store – where does it come from? There are undoubtedly hardworking people who farm, refine, etc. and when we walk into Sobey’s, there it is.

My appreciation of boats in the Caribbean has always been similarly vague. You get on the plane that in Tortola or Antigua, head down to the Cay and there it sits, gleaming and ready. The crew aboard is already sipping rum in the warm sunshine and all is divine.

Despite my decidedly myopic viewpoint on all this, the reality is those boats all came to paradise from somewhere. And that means someone brought them there. This is that story.

In late October when I arrive in Hampton VA to learn more, I walk into the middle of the Salty Dawg’s Halloween costume party. The crews have let their hair down (real and fake!) and the rum has clearly lubed the outfits. Big winners are the crew of Persistence, a Leopard 44, who are dressed as “Mixed Drinks” Mark Wormwood was the Black Russian, Bloody Mary the crew and so on.

But the merriment is only part of the Dawg culture, albeit a very important one. If you are a boat owner up here in the True North you know that getting to the wonderful cruising grounds of the Caribbean requires many inputs. Boating skill and experience in abundance and very detailed boat preparation are necessities for cruising enjoyment and particularly for safety. Weather information, sufficient supplies and good crew are also required. If you’ve elected to do the passage and can add 70 or so companion boats to your delivery complement, that’s even better.

Cruising rallies are the choice of many boaters heading to the warm, sparkling blue seas. There is some minor premise of winning the rally, but mostly it’s an opportunity to make the passage with others and celebrate when you arrive.

The longest standing rally is the very popular ARC Caribbean 1500 that traces its routes to England circa 1986. Each November its participants head from Portsmouth VA south to the British Virgin Islands.

As an alternative to that longstanding tradition, Bill and Linda Knowles of Bristol RI founded the Salty Dawg Rally in 2011 as a grassroots (read low cost) way to achieve similar ends. Every year since boaters assemble in hospitable Hampton Virginia to renew acquaintances, share knowledge and then prepare to the trip south. This includes a lot of camaraderie, but as I found out it also incorporates a lot of hard work and study. There’s also a healthy dose of shared caution and smarts. Using onboard technology, the Dawgs also track the progress of each boat on its Follow the Fleet page, with a live chart that lets friends and relatives follow each boat’s progress. There’s also opportunity for blogging on the Dawg site.

You’ll find a good helping of Canadian content among the Salty Dawgs. I don’t have to tell you that over our boating histories, each and every one of us has contemplated heading over the horizon and some of us even turn that dream into reality. They can purchase a boat somewhere in the south or make their way down the US east coast to join the Rally for its departure in early November.

I sat with Vancouver’s Paul and Gwyn Wagschal and their dog Charlie Echo (Director of Security) at the final weather seminar when the prospects a tropical depression was discussed. This was just one of the many sessions that had packed the Dawg House prior to the targeted departure date and I was quite overwhelmed with the detail of the questions and the volume of information exchanged. Paul and Gwyn have achieved their dream - “a new direction in life" that you and I have discussed – but they are doing it. Check out their lives at svbluesky.com.

Be preparedThe sessions explore in detail everything from SSB communication to visa and immigration issues, the necessity of enrolling visiting grandchildren in school and where to store your dinghy. Tips were revealed on freezing food and how to deal with pets; garbage and its disposal. Frankly, some of it seemed more detailed than my day job.

I went aboard as SV Goose as Bob and Sue Webb from Winnipeg with their crew readied the Saga 43 for the passage. They spoke enthusiastically about their plan, but only pause the process of bringing supplies aboard briefly so I could take their photo with Lucy the wonder dog (a cute doggie with a cute name appears to be de rigeur for the passage).

When they emailed me in late November from BVI, their report made it clear all the prep was worthwhile.

We departed Hampton on Nov 3 around noon and arrived in Sopers Hole, Tortola early morning on Nov 14. Our passage was successful and without any major incidents – the usual chafed reefing line and broken block on the traveller kind of stuff but otherwise uneventful. The wind, however, was forward of the beam for the whole trip until it disappeared two days out of Tortola. We were predominantly hard on the wind and the boat was significantly heeled over most of the trip. We entered and exited the Gulf Stream using the waypoints provided by the Salty Dawg weather router, Chris Parker.

It’s not all sunshineToronto racer turned cruiser Brian Rutter retired in June 2015, then set out to cross items off his bucket list. In July six Mimico Cruising Club friends chartered Hula Girl, a Santa Cruz 50 and raced the 2500-mile Los Angeles to Hawaii Trans Pac. Then, Brian and Cathy purchased Salacia, a 2005 Beneteau First 44.7 and converted her to an ‘ocean read’ fast cruiser adding a desalinater, chart plotters, AIS, EPRIB, satellite phone, dodger, larger battery bank, solar panel bank, dinghy and davits, upgraded ground tackle … you get the picture. They motored 850 miles to Hampton via the Erie Canal and ICW arriving in early October

With an experienced crew they describe as FOG (four older guys), Salacia departed during a break in the nasty weather on November 1st. The stormy seas followed them most of the way and more than a few technical issues riddled the passage plus a long detour to avoid Tropical Storm Kate. But Salacia managed 200 miles a day and arrived in Tortola on Day 11, one of the first to complete the passage.

Beyond skill and preparation, a certain mindset seems to be required for this world cruising life. Meeting the Salty Dawgs and learning about their groundwork and expectations is truly a privilege and certainly one of the real benefits of participating in an event like this rally.

Staying onAfter saying goodbye in Hampton to keep her from thrashing through the passage, Bob and Sue Webb had Lucy fly down and meet them in BVI. They now plan to leave Goose in the Caribbean for a few years and explore the Caribbean.

And so it goes. Some Dawgs stay, some return in the Spring Rally back to Hampton. Some do it once and some every year, but there is a camaraderie that is unmistakable. The Dawgs meet in the BVI, at the Newport and Annapolis Boat Shows and elsewhere to swap tales and info. Salty Dawgs is a club, an educational resource and a safety society. For the Canadians and others who take part it’s a way to live the dream.

You’ll like Hampton too.The Salty Dawgs get a big welcome each autumn from Hampton Virginia and you can too. While heading down to the Caribbean is the golden ring of sailing into the sunset, a cruise down the Intracoastal in a nice trawler certainly has its appeal as well. Or, if you enjoy historical towns that love boats, you could even whip down by interstate to add some time near the pier to your season.

For a small place it’s pretty long on history and things to do, surrounded with a maritime theme. Situated where the Chesapeake Bay meets the Atlantic, it has been at the heart of America since 1609 when what is now Fort Monroe was built in Hampton Roads Harbour. Just across the way from Norfolk where the aircraft carriers and subs hang out, today Hampton combines a sense of history with a contemporary and charming small city, all overlooking the water. There are a dozen marinas including one right downtown, close to the pubs and some pretty delicious eating spots. Another nearby village-y area, Phoebus, is home to a couple more marinas and a funky canvas shop.

Also right downtown are the Hampton History Museum, St John’s Church, the oldest continuous English-speaking parish in the US and the Virginia Air & Space Center, the official showplace of NASA in nearby Langley. Its unrivalled jet and spacecraft collection includes the Apollo 12 command module and a three billion year old moon rock.

Perhaps slightly tamer is an old fashioned carousel built by the Philadelphia Toboggan Company and installed at Buckroe Beach on the Chesapeake in 1920. Today it has been relocated to the center of Hampton across from the Space Center, perhaps to demonstrate the ying and yang of transportation methods and contrast the old and new of the city.

Photo Captions:Photo 1 - Pirate costumes and dark ‘ n’ stormies are musts prior to departurePhoto 2 - Canadian flags dot the docks as the Dawgs prepare for departure.Photo 3 - Weather and routing briefings by forecaster Chris Parker glued the crews to the screenPhoto 4 - Fall view of Old Point Comfort Marina (location of The Deadrise Restaurant)Photo 5 - Boating centre Hampton has a perfect harbour right downtownPhoto 6 - since the Rally Departs just after Halloween, a costume party is definitely in orderPhoto 7 - Downtown Boat Basin with the Space Center behindPhoto 8 - Brandon Brittle of St George Brewing, Hamptom